2-(4-(Bromomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Base Information

• Chemical Name: 2-(4-(Bromomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS No.: 138500-85-3
• Molecular Formula: C13H18BBrO2
• Molecular Weight: 297
• Hs Code.: 29349990
• European Community (EC) Number: 679-122-7
• DSSTox Substance ID: DTXSID00395701
• Nikkaji Number: J903.148K
• Wikidata: Q72446665
• Mol file: 138500-85-3.mol

Synonyms:138500-85-3;2-(4-(Bromomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;4-(Bromomethyl)benzeneboronic acid pinacol ester;4-Bromomethylphenylboronic acid, pinacol ester;4-Bromomethylphenylboronic acid pinacol ester;2-[4-(bromomethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;4-(Bromomethyl)phenylboronic Acid Pinacol Ester;MFCD02179493;4-(Bromomethyl)benzeneboronic acid, pinacol ester;1,3,2-DIOXABOROLANE, 2-[4-(BROMOMETHYL)PHENYL]-4,4,5,5-TETRAMETHYL-;2-[4-(BROMOMETHYL)PHENYL]-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABORONATE;SCHEMBL104247;(4-(BROMOMETHYL)PHENYL)BORONIC ACID PINACOL ESTER;DTXSID00395701;4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl Bromide;BCP31413;AKOS015917391;AB11263;AM86576;AS-2400;CS-W002910;AC-30807;SY007915;4-(bromomethyl)phenylboronic pinacol ester;A2989;BB 0259741;FT-0643285;T2945;4-bromomethylphenyl boronic acid pinacol ester;(4-bromomethylphenyl)boronic acid pinacol ester;4-Bromomethyl phenyl boronic acid pinacol ester;EN300-124118;4-Bromomethylphenylboronic acid pinacol ester, 95%;J-007145;J-514828;Z1436659965;4-(BROMOMETHYL)BENZENEBORONIC ACID PINACOL ESTER, 95%;2-(4-Bromomethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-4-Bromome thylphenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolame;2-(4-Bromomethyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane;3-hydroxy-2,3-dimethylbutan-2-yl hydrogen 4-(bromomethyl)phenylboronate;4-Bromomethylphenylboronic Acid Pinacol Ester

Chemical Property of 2-(4-(Bromomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property:

• Vapor Pressure: 8.44E-05mmHg at 25°C
• Melting Point: 83-85 °C
• Refractive Index: 1.524
• Boiling Point: 351.2 °C at 760 mmHg
• Flash Point: 166.2 °C
• PSA: 18.46000
• Density: 1.26 g/cm³
• LogP: 2.88070
• Storage Temp.: Keep Cold
• Solubility.: soluble in Toluene
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 296.05832
• Heavy Atom Count: 17
• Complexity: 257

Purity/Quality:

98% ^*data from raw suppliers

2-[4-(Bromomethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-34
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC=C(C=C2)CBr
• Uses: 2-[4-(Bromomethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is used in the synthesis of metalloproteinase-13 inhibitors in the treatment of osteoarthritis.

Technology Process of 2-(4-(Bromomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

There total 24 articles about 2-(4-(Bromomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol (302348-51-2) → 4-bromomethylphenylboronic acid pinacol ester (138500-85-3)

Guidance literature:

With carbon tetrabromide; triphenylphosphine; In tetrahydrofuran; at 0 - 20 ℃; for 18h; Inert atmosphere;

Reference yield: 86.0%

p-tolylboronic pinacol ester (195062-57-8) → 4-bromomethylphenylboronic acid pinacol ester (138500-85-3)

Guidance literature:

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In cyclohexane; for 5h; Heating;

DOI:10.1055/s-2006-926234

Reference yield: 76.1%

N-Bromosuccinimide (128-08-5) + p-tolylboronic pinacol ester (195062-57-8) → 4-bromomethylphenylboronic acid pinacol ester (138500-85-3)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); In tetrachloromethane; for 14h; Reflux;

upstream raw materials:

2,3-dimethyl-2,3-butane diol

4-bromomethylphenylboronic acid

p-tolylboronic pinacol ester

(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol

Downstream raw materials:

4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]morpholine

B₁₀H₁₀C₂CH₃CH₂C₆H₄BO₂C₂(CH₃)4

4-((4-acetylpiperazin-1-yl)methyl)phenylboronic acid

tert-butyl 4-[[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl]piperazine-1-carboxylate

Refernces

• 1、 Powell, Chadwick R.,Dillon, Kearsley M.,Wang, Yin,Carrazzone, Ryan J.,Matson, John B.. "A Persulfide Donor Responsive to Reactive Oxygen Species: Insights into Reactivity and Therapeutic Potential". . p. 6324 - 6328. Retrieved 2018.
• 2、 Howard,Dong, Hui Fang,Oppenheim, Joost J.,Insaf, Shabana,Santhosh, Kalpathy C.,Paul, Gitendra,Cushman, Mark. "Inhibition of RANTES/CCR1-mediated chemotaxis by cosalane and related compounds". . p. 59 - 62. Retrieved 2001.
• 3、 -. "DRUG AND GENE THERAPY TO TREAT HIGH MYOPIA AND OTHER OCULAR DISORDERS WITH ENLARGED EYE GLOBES". Paragraph 0078; 0080. . Retrieved 2021/12/29.
• 4、 Mohite, Amar R.,Phatake, Ravindra S.,Dubey, Pooja,Agbaria, Mohamed,Shames, Alexander I.,Lemcoff, N. Gabriel,Reany, Ofer. "Thiourea-Mediated Halogenation of Alcohols". . p. 12901 - 12911. Retrieved 2020/11/26.